(S)-(-)-(Phenylsulfinyl)acetic acid | 60833-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(-)-(Phenylsulfinyl)acetic acid
• 英文别名: (S)-2-phenylsulfinylacetic acid；2-[(S)-phenylsulfinyl]acetic acid
• CAS: 60833-03-6
• 化学式: C₈H₈O₃S
• 分子量: 184.216
• InChiKey: PPAUMJSTRVZNNE-LBPRGKRZSA-N

物化性质

• 沸点：
  423.0±28.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (S)-(-)-(Phenylsulfinyl)acetic acid 生成 methyl (S)-2-phenylsulfinylacetate
  参考文献：
  名称：

  Microbial deracemization of α-substituted carboxylic acids: control of the reaction path

  摘要：

  A novel approach to preparing optically active alpha-substituted carboxylic acids using the whole cells of Nocardia diaphanozonaria JCM 3208 is described. When 2-phenylthiopropanoic acid and 2-methyl-3-phenylpropanoic acid were subjected to the reaction under aerobic conditions, the oxidation reaction proceeded preferentially rather than deracemization of these substrates. Herein, we report the design of reaction conditions to increase the deracemization activity in preference to oxidation reactions. In addition, we have successfully detected a metabolic intermediate in the reaction mixture of 2-methyl-3-plienylpropanoic acid, which indicates that the deracemization is a competitive reaction against the beta-oxidation pathway of fatty acid metabolism. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.049
• 作为产物：
  描述：

  苯基硫代乙酸甲酯 在 三甲基氯硅烷 、 双氧水 、 lipoprotein lipase from Burkholderia sp. (EC 3.1.1.3) 作用下， 以 aq. phosphate buffer 、 甲苯 、 乙腈 为溶剂， 反应 17.0h， 生成 (S)-(-)-(Phenylsulfinyl)acetic acid
  参考文献：
  名称：

  α-亚磺酰酯的酶促分离和脱羧官能团化

  摘要：

  α-亚爷酯的酶促分离得到具有高对映体纯度的回收酯和 α-亚爷酸。脱羧官能团化提供了两种对映体形式的多种光学活性亚砜。

  DOI：

  10.1002/chem.202302996

文献信息

• A facile route to homochiral sulfoxides
  作者：Kevin Burgess、Ian Henderson

  DOI：10.1016/s0040-4039(01)80467-6

  日期：1989.1

  Biocatalytic resolutions of methyl sulfinylacetates fford sulfoxides (R)-(1) - (6) in very high optical yields; the products have been used in a systematic study of the “SPAC” reaction, an asymmetric synthesis of γ-hydroxy-α,β-unsaturated esters.

  以非常高的光学收率得到亚甲基乙酸乙酸甲酯和亚砜（R）-（1）-（6）的生物催化拆分；该产品已用于系统研究“ SPAC”反应，即不对称合成γ-羟基-α，β-不饱和酯。
• Biocatalytic resolutions of sulfinylalkanoates: a facile route to optically active sulfoxides
  作者：Kevin Burgess、Ian Henderson、Kwok Kan Ho

  DOI：10.1021/jo00030a044

  日期：1992.2

  Two methods are presented for kinetic resolutions of compounds containing ester and sulfoxide functionalities (sulfinylalkanoates). In the first a crude lipase preparation from Pseudomonas sp. (K10) mediates enantioselective hydrolysis of these esters in an aqueous environment. The second method uses the same lipase preparation to promote enantioselective transesterifications with alcohols in hexane. Both procedures are suitable for preparation of sulfinylalkanoates where the ester and sulfoxide groups are separated by one or two methylene units (sulfinylacetates and sulfinylpropanoates) but compounds with three methylene "spacer groups" (sulfinylbutanoates) are not substrates for the lipase under either set of conditions.
• BURGESS, KEVIN;HENDERSON, IAN, TETRAHEDRON LETT., 30,(1989) N8, C. 3633-3636
  作者：BURGESS, KEVIN、HENDERSON, IAN

  DOI：——

  日期：——